Reactive polymers containing pendant azetidine or azetidinium functions, 1. Synthesis of poly(acrylic ester)s and poly(methacrylic ester)s of 1‐alkyl‐3‐hydroxyazetidines and related azetidinium salts

Abstract

Trans-esterification of methyl acrylate or methyl methacrylate with I-alkyl-3-azetidinols leads to the corresponding azetidinyl acrylates or methacrylates. These new monomers are polymerized by a free radical mechanism to polymers containing pendant azetidine functions. When these polymers are treated with a mineral acid or with a strong alkylating agent, such as dimethyl sulfate, water-soluble polymers are obtained. An alternative route is to transform the monomer into the azetidinium salt form and to polymerize this salt in aqueous solution. Azetidinium ion containing polymers are stable at room temperature but cross-link to insoluble materials above 120°C.